Ethyl Acetate → HCID 178450822, Verbindung

HRID 2169234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169234
[C:1]1([C:7]2[C:8]([CH2:13][C:14]([NH2:16])=[NH:15])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([O:21][C:22](=[O:37])/[C:23](/O)=[C:24](\[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)/[C:25](O)=[O:26])([CH3:20])([CH3:19])[CH3:18].C[O-].[Na+].C(OCC)(=O)C>CO.CCCCCC>[C:17]([O:21][C:22]([C:23]1[C:24]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:25]([OH:26])[N:16]=[C:14]([CH2:13][C:8]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)[N:15]=1)=[O:37])([CH3:20])([CH3:18])[CH3:19]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 867258802-(3-Phenyl-pyridin-2-yl)-acetamidineHCID 86725882(E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester

Produkt 1

HCID 178450822HCID 178450822, VerbindungAusbeute 48,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(3-phenyl-pyridin-2-yl)-acetamidine (162) (300 mg, 1.10 mmol) and (E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester (4) (511 mg, 1.66 mmol) in methanol (5 mL) was added sodium methoxide (1.3 mL, 3.32 mmol) at 0° C., then the reaction mixture was allowed to warm to room temperature, stirred for 16 h. Silica thin layer chromatography was performed (50% ethyl acetate in hexane, Rf=0.3). After completion of the reaction, it was quenched with water, methanol was evaporated and water (30 mL) was added. The mixture was extracted with ethyl acetate (3×30 mL) and the separated organic part was dried and concentrated to get a crude product, which was purified by a CombiFlash column (eluted at 90% ethyl acetate in hexane) to get 5-benzyloxy-6-hydroxy-2-(3-phenyl-pyridin-2-ylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (163) (250 mg, 48.1%) as a yellow sticky product.

Aufarbeitung

  1. customAfter completion of the reaction, it
  2. customwas quenched with water, methanol
  3. customwas evaporated
  4. additionwater (30 mL) was added
  5. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
  6. customthe separated organic part was dried
  7. concentrationconcentrated
  8. customto get a crude product, which
  9. customwas purified by a CombiFlash column (eluted at 90% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1d328b6d972445f8a104422304cd2968
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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